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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:10 UTC
HMDB IDHMDB0000426
Secondary Accession Numbers
  • HMDB00426
Metabolite Identification
Common NameCitramalic acid
DescriptionCitramalic acid, also known as citramalate or 2-methylmalate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Citramalic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563860650
Synonyms
ValueSource
(+-)-2-Hydroxy-2-methylsuccinic acidChEBI
2-Hydroxy-2-methylbutanedioic acidChEBI
2-Hydroxy-2-methylsuccinic acidChEBI
2-Methylmalic acidChEBI
alpha-Hydroxypyrotartaric acidChEBI
Citramalic acidsChEBI
(+-)-2-Hydroxy-2-methylsuccinateGenerator
2-Hydroxy-2-methylbutanedioateGenerator
2-Hydroxy-2-methylsuccinateGenerator
2-MethylmalateGenerator
a-HydroxypyrotartarateGenerator
a-Hydroxypyrotartaric acidGenerator
alpha-HydroxypyrotartarateGenerator
Α-hydroxypyrotartarateGenerator
Α-hydroxypyrotartaric acidGenerator
CitramalateGenerator
(b)-2-MethylmalateHMDB
(b)-2-Methylmalic acidHMDB
(b)-CitramalateHMDB
(b)-Citramalic acidHMDB
(R,S)-(b)-CitramalateHMDB
(R,S)-(b)-Citramalic acidHMDB
(R,S)-b-MethylmalateHMDB
(R,S)-b-Methylmalic acidHMDB
(R,S)-beta-MethylmalateHMDB
(R,S)-beta-Methylmalic acidHMDB
2-Deoxy-3-C-methyltetrarateHMDB
2-Deoxy-3-C-methyltetraric acidHMDB
2-Hydroxy-2-methyl-(b)-butanedioateHMDB
2-Hydroxy-2-methyl-(b)-butanedioic acidHMDB
2-Hydroxy-2-methyl-butanedioateHMDB
2-Hydroxy-2-methyl-butanedioic acidHMDB
2-Methyl-(b)-malateHMDB
2-Methyl-(b)-malic acidHMDB
DL-CitramalateHMDB
DL-Citramalic acidHMDB
Citramalate, (+-)-isomerHMDB
Citramalate, (R)-isomerHMDB
Citramalate, (S)-isomerHMDB
alpha-MethylmalateHMDB
Citramalic acidKEGG
(R)-2-Hydroxy-2-methylbutanedioateGenerator
Chemical FormulaC5H8O5
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
IUPAC Name2-hydroxy-2-methylbutanedioic acid
Traditional Namecitramalate, (+-)-
CAS Registry Number597-44-4
SMILES
CC(O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)
InChI KeyXFTRTWQBIOMVPK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107 - 111 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility297 g/LALOGPS
logP-0.91ALOGPS
logP-0.68ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.59 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-9200000000-d88cf81bb63b8badd74dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00gs-8492000000-d1c8fb9235f1de536d15JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000j-7900000000-efbe2adf2c82decc64a6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-052u-9000000000-3754186783f820cbff7cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052o-9000000000-0656e8e194378442727fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-2900000000-be1cc6b0ea685f5d7ac2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-002r-8900000000-7dd192ed79cd2d306ea5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9500000000-c96a62314140c10f1245JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-5900000000-437d36fe16a8d6f79c68JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9200000000-6aed3a8e654948bbd5e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-31c6a41b79f5b68fa431JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uds-4900000000-0d782e5134753ac75aebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-9800000000-79154974b5c30f915ea5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-16648250719da0016f96JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Infant (0-1 year old)Both
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified2.5-4.5 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified2.4 (1.0-4.8) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified2.5-3.4 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified3.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified14.0 (5.5-24.6) umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal details
    UrineDetected and Quantified11.8 (5.5-21.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
    UrineDetected and Quantified5.5 (4.2-8.9) umol/mmol creatinineChildren (1-13 years old)BothNormal details
    UrineDetected and Quantified4.7 (1.3-11.2) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB002815
    KNApSAcK IDC00001181
    Chemspider ID1051
    KEGG Compound IDC00815
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5415
    PubChem Compound1081
    PDB IDNot Available
    ChEBI ID15584
    Food Biomarker OntologyNot Available
    VMH IDCITMAL
    References
    Synthesis ReferenceBarker, H. A. Chemical synthesis and resolution of (±)-citramalic acid. Biochemical Preparations (1962), 9 25-9.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. HULME AC: The oxidation of citramalic acid and beta-hydroxyglutaric acid to acetoacetic acid and the possible significance of citramalic acid in plant metabolism. Biochim Biophys Acta. 1954 May;14(1):44-51. [PubMed:13160012 ]
    2. Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]
    3. Perlman S, Carr SA: Citramalic acid in cerebrospinal fluid of patients with bacterial meningitis. Clin Chem. 1984 Jul;30(7):1209-12. [PubMed:6145530 ]
    4. Greter J, Lindstedt S, Seeman H, Steen G: 2-hydroxy-2-methylsuccinic acid--a urinary metabolite in propionyl-CoA carboxylase deficiency. Clin Chim Acta. 1980 Sep 8;106(1):103-6. [PubMed:7408203 ]
    5. Shaw W, Kassen E, Chaves E: Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features. Clin Chem. 1995 Aug;41(8 Pt 1):1094-104. [PubMed:7628083 ]